Potassium Carbonate → 5-amino-3-[(2R,3R,5S)-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione

HRID 60747Notes

Reaction equation

HRID 60747 reaction equation
C([O:9][C@H:10]([C@@H:13]1[CH2:17][C@@H:16]([CH3:18])[C@H:15]([N:19]2[C:23]3[N:24]=[C:25]([NH2:29])[NH:26][C:27](=[O:28])[C:22]=3[S:21][C:20]2=[O:30])[O:14]1)[CH2:11][CH3:12])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[NH2:29][C:25]1[NH:26][C:27](=[O:28])[C:22]2[S:21][C:20](=[O:30])[N:19]([C@H:15]3[C@H:16]([CH3:18])[CH2:17][C@@H:13]([C@@H:10]([OH:9])[CH2:11][CH3:12])[O:14]3)[C:23]=2[N:24]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 137108705[(1S)-1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-methyl-tetrahydrofuran-2-yl]propyl] benzoate2×

Product 1

HCID 1371086925-amino-3-[(2R,3R,5S)-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dioneYield 27.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound [(1S)-1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-methyl-tetrahydrofuran-2-yl]propyl] benzoate (compound 28k-A, 120 mg, 0.27 mmol) in MeOH (2 mL) was added K2CO3 (58 mg, 0.42 mmol). After being stirred at room temperature for 5 hours, the reaction mixture was adjusted to pH 7 by bubbling CO2 and then concentrated in vacuo. The residue was purified by preparative HPLC to afford 24 mg of 5-amino-3-[(2R,3R,5S)-5-[(1S)-1-hydroxypropyl]-3-methyl-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (Example 28) as a white solid.

Workup

  1. customby bubbling CO2
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-07c9cbdd29524dcca6a1f8a6a8b8556f
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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